MoviesThe Matrix (1999): Neo's journey from believing the world is real to seeing the code behind the illusion is the ultimate "red pill" metaphor. It forces a complete reevaluation of reality, choice, and freedom.
It's a Wonderful Life (1946): George Bailey sees what the world would be like without him. Classic perspective shift on personal value and the ripple effects of everyday life.
Groundhog Day (1993): Phil Connors is forced to relive the same day until he changes as a person. Great for showing how shifting from selfishness to empathy transforms everything.
Life is Beautiful (1997): A father reframes the horrors of a concentration camp as a game to protect his son. Profound example of choosing perspective as an act of love and survival.
American Beauty (1999): Lester Burnham's midlife crisis leads to a radical shift in what he values. The famous plastic bag scene (and the ending narration) is a direct meditation on finding beauty and meaning in the mundane.
TV EpisodesThe Twilight Zone has dozens, but especially:"Eye of the Beholder" (beauty standards and how society defines "normal")
"The Masks" (a dying man forces his greedy family to wear masks that reveal their true natures)
Star Trek: The Next Generation - "The Inner Light" (Picard lives an entire lifetime in minutes as a man on a dying planet, completely changing how he views legacy and time).
BoJack Horseman - Multiple episodes, but especially the "Fish Out of Water" underwater episode (silent, forces you to experience BoJack's isolation differently) and "Time's Arrow" (dementia and family perspective).
OtherAnthony Bourdain's Parts Unknown (whole series): You already mentioned him — his travel philosophy is perfect. He repeatedly showed how stepping into other cultures dismantles your assumptions.
The Shawshank Redemption: Andy Dufresne's quiet refusal to let prison break his spirit, culminating in his escape and the letter about hope. "Get busy living or get busy dying."
Dead Poets Society (which you mentioned): "Carpe Diem" + standing on the desk scene = literally changing the angle from which you see the world.
Books that translate well to film/discussion: The Alchemist (following your personal legend changes how you see obstacles) or Siddhartha (the river teaches that everything is connected).